Synthetic and 1 H and 13 C NMR Spectral Studies on N-(Mono-substitutedphenyl)-acetamides H 4. NH-CO- CH 3 i. ; X = Cl, CH 3
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1 Synthetic and 1 H and 13 C NMR Spectral Studies on N-(Mono-substitutedphenyl)-acetamides and Substituted Acetamides, 2/3/4-YC 6 H 4 NH-CO- CH 3 i X i (Y=CH 3, F, Cl, Br, NO 2 ; X = Cl, CH 3 ; i =0,1,2,3) Basavalinganadoddy Thimme Gowda, Shilpa, and Jayalakshmi K. Lakshmipathy Department of Post-Graduate Studies and Research in Chemistry, Mangalore University, Mangalagangotri , Mangalore, India Reprint requests to Prof. B. T. G.; Fax: ; gowdabt@yahoo.com Z. Naturforsch. 61a, (2006); received July 19, 2006 Nineteen N-(2/3/4-methyl/halo/nitro-phenyl)-acetamides and substituted acetamides, 2/3/4- YC 6 H 4 NH- (Y=CH 3, F, Cl, Br or NO 2 ;X=ClorCH 3 and i =0,1,2or3),have been prepared, characterized, and their 1 H and 13 C NMR spectra in solution measured and correlated. 1 H and 13 C NMR chemical shifts were assigned to the protons and carbon atoms, respectively, in line with those for similar compounds. Since the chemical shifts are dependent on the electron density around the nucleus or associated with the atom to which it is bound, the incremental shifts of the aromatic protons or carbon atoms due to -NH- and (X = Cl or CH 3 and i =0,1,2,3)inalltheN-phenyl-substituted acetamides, C 6 H 5 NH-, are calculated by comparing the proton or carbon chemical shifts of these compounds with those of benzene or aniline. The incremental shifts due to the groups in the parent compounds have also been computed by comparing the chemical shifts of the protons or carbon atoms in these compounds with those of benzene or aniline, respectively. The computed incremental shifts and other data were used to calculate the 1 H and 13 C NMR chemical shifts of the substituted compounds in three different ways. The calculated chemical shifts by the three methods compared well with each other and with the observed chemical shifts, testing the validity of the principle of additivity of the substituent effects in these compounds. The variation of 1 H NMR chemical shifts of either the aromatic or N-H protons, with the substituents in N-(phenyl)- and N-(2/3/4-chloro/methylphenyl)-acetamides and substituted acetamides did not follow the same trend, while the variation of the 13 C NMR chemical shifts of C-1 and C=O carbon atoms and those of alkyl carbon atoms of these compounds followed more or less the same trend. Key words: 1 H and 13 C NMR Spectra; N-Aryl-acetamides; N-Aryl-substituted Acetamides. 1. Introduction The amide moiety is an important constituent of many biologically significant compounds [1]. Thus an understanding of the formation, properties and reactions of amides is central to future development in such areas as polypeptide and protein chemistry. Many imides, hydroxamic acids and hydrazides exhibit pharmacological activity, which has further stimulated recent interest in their chemistry. Further, many acetanilides exhibit fungicidal, herbicidal and pharmacological activities. We have recently reported the infrared, Raman [2], NMR [3] and NQR [4] spectra and crystal structures [5] of several N-(aryl)-acetamides and substituted acetamides. As part of these efforts of correlating spectroscopic parameters with the chem- ical bond parameters, amides of the formulae 2/3/4- YC 6 H 4 NH- (Y = CH 3, F, Cl, Br or NO 2 ; X=ClorCH 3 and i = 0, 1, 2 or 3) have been prepared, characterized, their NMR spectra measured in solution and correlated. 2. Experimental 2.1. Materials and Methods N-Phenyl- and N-(2/3/4-methyl/halo/nitro-phenyl)- acetamides/substituted acetamides of the general formulae C 6 H 5 NH- and 2/3/4-YC 6 H 4 NH- (where Y = CH 3, F, Cl, Br or NO 2 ;X= Cl or CH 3 and i = 0, 1, 2 or 3) (Table 1) were prepared from substituted anilines, substituted acetic acids (Aldrich, Germany) and thionyl chloride [2 7] / 06 / $ c 2006 Verlag der Zeitschrift für Naturforschung, Tübingen
2 596 B. T. Gowda et al. N-(Mono-substituted-phenyl)-acetamides and Substituted Acetamides Table 1. Melting points (M. p.) and N-H and C=O infrared absorption frequencies of N-(substituted-phenyl)-substituted acetamides, j-yc 6 H 4 NH-. j-y, CH 3 i X i Compound M. p. ( C) γ N H (str) (cm 1 ) γ C=O (str) (cm 1 ) 2-NO 2,CH 3 N-(2-Nitrophenyl)-acetamide s s 3-NO 2,CH 3 N-(3-Nitrophenyl)-acetamide s s 4-NO 2,CH 3 N-(4-Nitrophenyl)-acetamide s s 4-F, CH 3 N-(4-Fluorophenyl)-acetamide s s 4-Br, CH 3 N-(4-Bromophenyl)-acetamide s s 3-Cl, CH 3 N-(3-Chlorophenyl)-acetamide s s 3-Cl, CH 2 Cl N-(3-Chlorophenyl)-2-chloroacetamide s s 3-Cl, CHCl 2 N-(3-Chlorolphenyl)-2,2-dichloroacetamide s s 3-Cl, CCl 3 N-(3-Chlorolphenyl)-2,2,2-trichloroacetamide s s 3-Cl, CH 2 CH 3 N-(3-Chlorophenyl)-2-methylacetamide s s 3-Cl, CH(CH 3 ) 2 N-(3-Chlorophenyl)-2,2-dimethylacetamide s s 3-Cl, C(CH 3 ) 3 N-(3-Chlorophenyl)-2,2,2-trimethylacetamide s s 3-CH 3,CH 3 N-(3-Methylphenyl)-acetamide s s 3-CH 3,CH 2 Cl N-(3-Methylphenyl)-2-chloroacetamide s s 3-CH 3, CHCl 2 N-(3-Methylphenyl)-2,2-dichloroacetamide s s 3-CH 3, CCl 3 N-(3-Methylphenyl)-2,2,2-trichloroacetamide s s 3-CH 3,CH 2 CH 3 N-(3-Methylphenyl)-2-methylacetamide s s 3-CH 3, CH(CH 3 ) 2 N-(3-Methylphenyl)-2,2-dimethylacetamide s s 3-CH 3, C(CH 3 ) 3 N-(3-Methylphenyl)-2,2,2-trimethylacetamide s s s, Strong. Table 2. 1 H NMR chemical shifts (δ, ppm) of various aromatic and other protons in N-(3-chloro-/3-methyl-phenyl)- substituted acetamides, 3-Cl/3-CH 3 C 6 H 4 NH-. H-2 H-4 H-5 H-6 N-H Alkyl H 3-ClC 6 H 4 NH- CO-CH d 7.04d 7.17t 7.66s CO-CH 2 Cl 7.59s 7.23d 7.27d 7.62d CO-CHCl m 7.14m 7.25t 7.64t CO-CCl s 7.29s 7.31s 7.70s 10.4 CO-CH 2 CH d 7.03d 7.17t 7.65s , 1.20 CO-CH(CH 3 ) d 7.03d 7.16t 7.68s , 1.20 CO-C(CH 3 ) d 7.00d 7.13t 7.65s H CH 3 C 6 H 4 NH- CO-CH t 6.89d 7.15t 7.34s , 2.09 CO-CH 2 Cl 7.21s 6.95d 7.17d 7.32t , 4.11 CO-CHCl t 6.95s 6.98s 7.35d , 6.27 CO-CCl s 7.03d 7.26m 7.39d CO-CH 2 CH s 6.87d 7.14t 7.34d , 2.22, 1.18 CO-CH(CH 3 ) t 6.89d 7.16t 7.41s , 2.21, 1.21 CO-C(CH 3 ) d 6.87d 7.14t 7.41s , 1.27 H The commercial anilines (Sisco Research Laboratories, India) were purified by either double distillation or zone refining. All other reagents employed in the preparations and purification of reagents were of analytical grade. Pure samples of the respective anilines (aniline, 2-methylaniline, 2-chloroaniline, 2- nitroaniline, 3-methylaniline, 3-chloroaniline, 3-nitroaniline, 4-methylaniline, 4-fluoroaniline, 4-chloroaniline, 4-bromoaniline or 4-nitroaniline) were treated Table 3. 1 H NMR chemical shifts (δ, ppm) of various aromatic and other protons in N-(substituted-phenyl)- acetamides, j-yc 6 H 4 NH-CO-CH 3. j-y H-2 H-3 H-4 H-5 H-6 N-H Alkyl H 2-Cl [3] 7.30d 7.16t 7.17d 8.10d Cl 7.33d 7.04d 7.17t 7.66s Cl [3] 7.58d 7.22d 7.22d 7.58d CH 3 [3] 7.22d 7.10t 7.00t 7.54d , CH t 6.89d 7.15t 7.34s , CH 3 [3] 7.39d 7.06d 7.06d 7.39d , NO d 7.15t 7.61t 8.16d NO d 8.17m 7.16m 7.63m NO m 8.13m 8.13m 7.82m F 7.45m 6.97m 6.97m 7.45m Br 7.42d 7.26s 7.26s 7.42d Table 4. 1 H NMR chemical shifts (δ, ppm) of various aromatic and other protons in N-(phenyl)-substituted acetamides, C 6 H 5 NH- (X = Cl, CH 3 ; i =0,1, 2, 3). H-2,6 H-3,5 H-4 N-H Alkyl H CO-CH d 7.20t 7.02t CO-CH 2 Cl 7.47d 7.27t 7.10t CO-CHCl d 7.32t 7.17t CO-CCl d 7.33t 7.18t 8.48 CO-CH 2 CH d 7.22t , 1.15 CO-CH(CH 3 ) d 7.26t 7.06t , 1.20 CO-C(CH 3 ) d 7.22t 7.01t H with mixtures of respective acetic acids (acetic acid, 2-chloroacetic acid, 2,2-dichloroacetic acid, 2,2,2-tri-
3 B. T. Gowda et al. N-(Mono-substituted-phenyl)-acetamides and Substituted Acetamides 597 NH- H-2,6 H-3,5 H-4 COCH 3 i X i H-2,6 H-3,5 H-4 NH-CO-CH CO-CH NH-CO-CH 2 Cl CO-CH 2 Cl NH-CO-CHCl CO-CHCl NH-CO-CCl CO-CCl NH-CO-CH 2 CH CO-CH 2 CH NH-CO-CH(CH 3 ) CO-CH(CH 3 ) NH-CO-C(CH 3 ) CO-C(CH 3 ) Table 5. The incremental chemical shifts (δ, ppm) of aromatic protons due to the groups NH- and - in C 6 H 5 NH- (X = Cl, CH 3 ; i =0,1,2,3). chloroacetic acid, 2-methylacetic acid, 2,2-dimethylacetic acid or 2,2,2-trimethylacetic acid) and thionyl chloride with constant stirring. The resulting mixtures were slowly warmed to expel HCl. Excess thionyl chloride was hydrolyzed by adding cold water dropwise under ice cold conditions. The solids separated were filtered under suction, washed thoroughly with water and dried. N-Phenyl- and N-(2/3/4- methyl/halo/nitro-phenyl)-acetamides/substituted acetamides could also be prepared by treating the respective anilines with the corresponding chloroacetyl chlorides in acetone or benzene. HCl produced was removed by treating with 2 M NaOH. The N-aryl-substituted acetamides thus prepared were recrystallized from ethanol several times to constant melting points. The compounds have been characterized by determining their melting points and by recording their infrared spectra and comparing with the literature values (Table 1) Spectral Measurements The 1 H and 13 C NMR spectra of all the N-(2/3/4- methyl/halo/nitro-phenyl)-acetamides and substituted acetamides were measured on a BRUKER Ac 300F, 300 MHz FT-NMR spectrometer. The spectra were recorded in CDCl 3 and DMSO with tetramethylsilane [(CH 3 ) 4 Si] as internal standard. 3. Results and Discussion H NMR Spectra 1 H NMR chemical shifts of aromatic and alkyl protons of all the N-(2/3/4-methyl/halo/nitro-phenyl)- acetamides and substituted acetamides are shown in Tables 2 4. The various chemical shifts were assigned to the protons in line with those for similar compounds [3]. Since the chemical shift depends on the electron density around the nucleus or associated with the atom to which it is bound, the incremental shifts of the aromatic protons (ppm) due to -NH-CO- CH 3 i X i (where X = Cl or CH 3 and i =0,1,2,3) in all the N-phenyl-substituted acetamides, C 6 H 5 NH-, were computed by comparing the proton chemical shifts of these compounds (Table 4) [3] with those of the benzene proton value of 7.27 ppm (Table 5). Similarly, the incremental shifts of the aromatic protons (ppm) due to (where X = Cl or CH 3 and i = 0, 1, 2 or 3) of these compounds were also computed by comparing their proton chemical shifts with those of the aniline proton values of H-2,6 = 6.48 ppm, H-3,5 = 7.05 ppm, H-4 = 6.67 ppm (Table 5). The chemical shifts of all the aromatic protons in all the N-(2/3/4-methyl/halo/nitro-phenyl)-acetamides and substituted acetamides, 2/3/4-YC 6 H 4 NH-CO- CH 3 i X i (where Y = CH 3, F, Cl, Br or NO 2 ;X=Cl or CH 3 and i = 0, 1, 2 or 3) were then calculated in three ways by adding either the substituent contributions [8] to the corresponding 1 H NMR chemical shifts of N-phenyl-substituted acetamides (Table 4) [3] or by adding the incremental shifts due to NH- or groups (Table 5) to the 1 H NMR chemical shifts of protons of the corresponding substituted benzenes or anilines, respectively. The calculated chemical shifts by the three procedures of calculation (values not shown) led to almost the same values and were in good agreement with the experimental chemical shifts, indicating that the validity of the principle of additivity of the substituent effects is quite good with these compounds C NMR Spectra The measured 13 C NMR chemical shifts of the aromatic and alkyl carbon atoms of all the N-(2/3/4- methyl/halo/nitro-phenyl)-acetamides and substituted acetamides are shown in Tables 6 8. The various chemical shifts are assigned to the different carbon atoms in the benzene rings in conformity with the literature for similar compounds [2, 3]. The 13 C NMR
4 598 B. T. Gowda et al. N-(Mono-substituted-phenyl)-acetamides and Substituted Acetamides 3-ClC 6 H 4 NH- (X = Cl, CH 3 ; i =0,1,2,3) C-1 C-2 C-3 C-4 C-5 C-6 C=O Alkyl C CO-CH CO-CH 2 Cl CO-CHCl CO-CCl CO-CH 2 CH , 9.6 CO-CH(CH 3 ) , 19.5 CO-C(CH 3 ) , 27.3 H CH 3 C 6 H 4 NH- (X = Cl, CH 3 ; i =0,1,2,3) CO-CH , 21.4 CO-CH 2 Cl , 21.3 CO-CHCl , 21.3 CO-CCl , 21.4 CO-CH 2 CH , 21.3, 9.7 CO-CH(CH 3 ) , 21.4, 19.6 CO-C(CH 3 ) , 27.4, 21.3 H Table C NMR chemical shifts (δ, ppm) of N-(3- chloro-phenyl)-substituted acetamides. Table C NMR chemical shifts (δ, ppm) of N-(substituted-phenyl)-acetamides, j-yc 6 H 4 NH-CO-CH 3. j-y C-1 C-2 C-3 C-4 C-5 C-6 C=O Alkyl C 2-Cl [3] Cl Cl [3] CH 3 [3] , CH , CH 3 [3] , NO NO NO Br F chemical shifts of benzene, substituted benzenes, aniline and substituted anilines were also measured under identical conditions and data used for computation of incremental shifts. The incremental shifts of the aromatic carbon atoms (ppm) due to NH- (where X = Cl or CH 3 and i = 0, 1, 2 or 3) groups were computed by comparing the 13 C NMR chemical shifts of N-(phenyl)- substituted acetamides, C 6 H 5 NH- (where X=ClorCH 3 and i = 0, 1, 2 or 3) [3], with the benzene carbon value of ppm (Table 9). Similarly, the incremental 13 C NMR shifts of the aromatic carbon atoms due to (where X = Cl or CH 3 and i = 0, 1, 2, 3) groups in these compounds were computed by comparing their chemical shifts with those of the aniline carbon values of C-1 = ppm, C-2,6 = ppm, C-3,5 = ppm, C-4 = ppm (Table 9). Then the 13 C NMR chemical shifts of all the aromatic carbon atoms in all the N- Table C NMR chemical shifts (δ, ppm) of N-(phenyl)- substituted acetamides, C 6 H 5 NH- (X = Cl, CH 3 ; i =0,1,2,3). C-1 C-2,6 C-3,5 C-4 C=O Alkyl C CO-CH CO-CH 2 Cl CO-CHCl CO-CCl CO-CH 2 CH , 9.5 CO-CH(CH 3 ) , 19.6 CO-C(CH 3 ) , 27.2 H (2/3/4-methyl/halo/nitro-phenyl)-acetamides and substituted acetamides were calculated in three ways by adding either the substituent contributions [2, 3] to the 13 C NMR chemical shifts of N-(phenyl)-substituted acetamides (Table 8) or the incremental shifts due to NH- or groups (Table 9) to the 13 C NMR chemical shifts of the corresponding substituted benzenes or anilines, respectively. The calculated 13 C NMR chemical shifts by the three procedures of calculation led to almost the same values and were in good agreement with the experimental chemical shifts, indicating the validity of the principle of additivity of the substituent effects with these compounds. 4. Comparisons and Conclusions The variation of 1 H NMR chemical shifts of either the aromatic or N-H protons with the substituents in N-(phenyl)-, N-(2-chlorophenyl)-, N-(3-chlorophen-
5 B. T. Gowda et al. N-(Mono-substituted-phenyl)-acetamides and Substituted Acetamides 599 Table 9. The incremental shifts in chemical shifts of aromatic carbon atoms due to -NH- and - groups in N-(phenyl)-substituted acetamides, C 6 H 5 NH- (X = Cl, CH 3 ; i =0,1,2,3). NH- C-1 C-2,6 C-3,5 C-4 C-1 C-2,6 C-3,5 C-4 NH-CO-CH CO-CH NH-CO-CH 2 Cl CO-CH 2 Cl NH-CO-CHCl CO-CHCl NH-CO-CCl CO-CCl NH-CO-CH 2 CH CO-CH 2 CH NH-CO-CH(CH 3 ) CO-CH(CH 3 ) NH-CO-C(CH 3 ) CO-C(CH 3 ) yl)- and N-(4-chlorophenyl)-, N-(2-methylphenyl)-, N-(3-methylphenyl)- and N-(4-methylphenyl)-acetamides and substituted acetamides did not follow the same trend, while the variation of 13 C NMR chemical shifts of C-1 carbon atoms of these compounds followed more or less the same trend. The variations of 13 C NMR chemical shifts of C=O carbon atoms and those of alkyl carbon atoms of the above compounds also followed similar trends. Acknowledgement The authors thank the Sophisticated Analytical Instrumentation Facility, Punjab University, Chandigarh , India, for the 1 H and 13 C NMR measurements. [1] J. Jabicky (Ed.), The Chemistry of Amides, Interscience, London 1970; R. Sandler and W. Karo, Organic Functional Group Preparations, Vol. 3, Academic Press, London [2] D. K. Bhat and B. T. Gowda, J. Indian Chem. Soc. 77, 279 (2000); 79, 163 (2002); B. H. A. Kumar and B. T. Gowda, J. Indian Chem. Soc. 79, 231 (2002); B. T. Gowda, K. Jyothi, K. L. Jayalakshmi, and N. Damodara, J. Indian Chem. Soc. 82, 564 (2005). [3] B. T. Gowda, K. M. Usha, and K. L. Jayalakshmi, Z. Naturforsch. 58a, 801 (2003); B. T. Gowda, K. M. Usha, and K. Jyothi, Z. Naturforsch. 59a, 69 (2004). [4] B. T. Gowda and A. Weiss, Z. Naturforsch. 49a, 695 (1994); B. T. Gowda, S. Dou, and A. Weiss, Z. Naturforsch. 51a, 627 (1996); B. T. Gowda, D. K. Bhat, H. Fuess, and A. Weiss, Z. Naturforsch. 54a, 261, 679 (1999); B. T. Gowda, B. H. A. Kumar, and H. Fuess, Z. Naturforsch. 55a, 721 (2000). [5] B. T. Gowda, S. Dou, and A. Weiss, Z. Naturforsch. 51a, 627 (1996); B. T. Gowda, H. Paulus, and H. Fuess, Z. Naturforsch. 55a, 711, 791 (2000); 56a, 386 (2001); B. T. Gowda, I. Svoboda, and H. Fuess, Z. Naturforsch. 55a, 779 (2000); 59a, 845 (2004); B. T. Gowda, K. Jyothi, H. Paulus, and H. Fuess, Z. Naturforsch. 58a, 225 (2003). [6] A. J. Hill and E. B. Kelsey, J. Am. Chem. Soc. 44, 2357 (1922). [7] W. Pies, H. Rager, and A. Weiss, Org. Magn. Reson. 3, 147 (1971). [8] R. M. Silverstein, G. C. Bassler, and T. C. Morrill, Spectrometric Identification of Organic Compounds, Wiley, New York 1991; W. Kemp, Organic Spectroscopy, MacMillan, London 1996.
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